Trifluoroacetic acid → HCID 178448632, compound

HRID 43289Notes

Reaction equation

HRID 43289 reaction equation
C(OC([NH:8][C:9]([CH3:44])([C:11]([O:13][C@@H:14]([CH3:43])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=1[C:27](/[N:29]=[C:30]1\[S:31][C:32]2[CH:37]=[CH:36][N:35]=[CH:34][C:33]=2[N:38]\1[CH2:39][CH2:40][CH2:41][CH3:42])=[O:28])=[O:12])[CH3:10])=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:44][C:9]([C:11]([O:13][C@@H:14]([CH3:43])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=1[C:27](/[N:29]=[C:30]1\[S:31][C:32]2[CH:37]=[CH:36][N:35]=[CH:34][C:33]=2[N:38]\1[CH2:39][CH2:40][CH2:41][CH3:42])=[O:28])=[O:12])([CH3:10])[NH2:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 178448631HCID 178448631, compound

Product 1

HCID 178448632HCID 178448632, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 2A (265 mg, 0.415 mmol) in anhydrous dichloromethane (4 mL) was added trifluoroacetic acid (Aldrich, 0.320 mL, 4.15 mmol). The solution was stirred at room temperature overnight, then saturated sodium bicarbonate solution was added to adjust the pH to 9. The mixture was extracted with dichloromethane (3×15 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated by rotary evaporator. Purification by flash chromatography (silica gel: 50-100% ethyl acetate in hexanes) afforded 202 mg (90%) of the title compound. 1H NMR (DMSO-d6) δ 0.94 (t, J=7.3 Hz, 3H), 1.08 (s, 3H), 1.10 (s, 3H), 1.30 (d, J=6.8 Hz, 3H), 1.34-1.46 (m, 3H), 1.77-1.87 (m, 3H), 4.19-4.32 (m, 2H), 4.53 (t, J=7.3 Hz, 2H), 5.08-5.18 (m, 1H), 7.39 (d, J=8.8 Hz, 1H), 7.84 (dd, J=8.6, 2.2 Hz, 1H), 8.03 (d, J=4.4 Hz, 1H), 8.23 (d, J=2.0 Hz, 1H), 8.50 (d, J=5.1 Hz, 1H), 9.03 (s, 1H). MS (ESI+) m/z 539 (M+H)+.

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×15 mL)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporator
  5. customPurification by flash chromatography (silica gel: 50-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-522632f6ad184038b6876b865171adf1
Source dataset
uspto-grants-2013_09
Patent number
US08536336B2

Reaction notes

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